PHILADELPHIA – Mixed in with the Flyers' rich history, which includes 37 postseason appearances in 46 seasons, eight trips to the finals and two Stanley Cups, their management team has made big mistakes.

For instance, Bob Clarke really goofed judging what Patrick Sharp could turn into in December 2005. Just 23 at the time, the speedy winger with a lot of offensive skill was dealt to the Chicago Blackhawks with throw-in forward Eric Meloche for forward Matt Ellison and a third-round pick.

Ellison quickly became a bust in a 43-game NHL career that included three goals, while Sharp went on to become a superstar for a Blackhawks franchise that is gunning for its second Cup in a row and third in five seasons.

Paul Holmgren, Clarke’s successor, made a few head-scratching deals, too, during his eight-year run as GM that ended May 7 when he was promoted to team president.

Here are our choices for the 10 worst of the 60 deals Holmgren made when running the Flyers:

1. THE START OF A BRYZASTER
Date: June 7, 2011Deal: Flyers acquire rights to free agent goalie Ilya Bryzgalov from Phoenix for minor-league LW Matt Clackson, a 2012 third-round pick and a conditional 2011 third-round pick (conditions met by Bryzgalov signing with Flyers before 2011 draft).Analysis: What a mess this was from start to finish, and after two disappointing and bizarre seasons, Flyers management was so desperate to get rid of Bryzgalov that it used a compliance buyout on him in which it was sparred his cap hit but forced to play him $1.64 million for 14 seasons from 2013-14 through 2026-27. This ordeal began with Holmgren trading for the rights to Bryzgalov 24 days before he’d hit the unrestricted free-agent market, then quickly led to a nine-year, $51-million contract. Did Flyers chairman Ed Snider pressure Holmgren to do this trade-and-sign? He says no, but Snider was pretty fed up watching the Flyers’ two-round 2011 playoff run in which three goalies were used. Holmgren was pressured to find a new No. 1 goalie, and at the time, Bryzgalov was the best available. The problem here is that Flyers management - and we’ll blame Holmgren because he was the GM - either didn't conduct a thorough investigation or ignored its findings on what kind of teammate Bryzgalov was. He was so despised in Phoenix that former teammates ripped him publicly after he left. In Philadelphia, Bryzgalov’s very different personality ignited constant controversy inside and outside the dressing room. That along with too much inconsistent play led to a quickie divorce.

2. JVR FOR LUKE
Date: June 23, 2012Deal: Flyers trade LW James van Riemsdyk to Toronto for D Luke Schenn.Analysis: This rumored deal involving top five overall draft picks who had disappointing starts to their NHL careers went down a few hours after the 2012 draft. Two seasons later, the Flyers surely would love a mulligan on this one because their top line with center Claude Giroux and right wing Jakub Voracek is missing a big and fast left winger who can score like JVR, who had a career-best 30 goals in a 2013-14 season in which Schenn struggled. At the time of the trade, it looked like a needed change for both players. Schenn, the fifth overall pick in 2008, was moved to a team desperate for a talented young blueliner and he'd get a chance to play with his little brother, Flyers forward Brayden Schenn. Van Riemsdyk, a Jersey boy who was the second pick in 2007, was coming off an injury-riddled season in which he saw a lot of time on the third line when healthy. So far, the Leafs are big winners in this deal. Schenn still is a big hitter and plays hard, but he's prone to mistakes, doesn’t provide much offense and he hasn't come close to fulfilling expectations of developing into a star. The Flyers would settle for a consistent second-pair defenseman, and thus far they haven’t gotten that. It still could happen: Schenn is just 24. But while the Flyers are waiting, hoping and paying Schenn a lot of money, JVR, 25, has become a star.

3. BLEW SHOT AT CARLSON
Date: June 20, 2008Trade: Flyers deal 2008 first-round pick (27th overall) to Washington for D Steve Eminger and a 2008 third-round pick (84th overall).Analysis: The Flyers were on the clock for their first pick of the 2008 draft, and still there for the taking was defensive prospect John Carlson. The Flyers had tried to trade up earlier in the draft, but stayed put until being suckered into a deal with the Capitals in which they acquired Eminger and a No. 3 for their No. 1. The Flyers thought they were getting a solid second-pair defenseman. They were wrong. Although a big guy and good skater, Eminger wound up being a defensive liability who provided no offense. The Flyers gave up on him very quickly, as Eminger was traded early into his first season with the team after playing just 12 games. Meantime, the Caps used the Flyers’ No. 1 to draft Carlson, who quickly developed into something special as a 6-foot-3 shutdown defenseman who plays big minutes. He was a first-team All-Rookie in 2010-11 and this season represented Team USA at the Sochi Olympics. Here's what Adam Oates, recently fired as the Caps' coach, said about Carlson this season, "He's one of the best defensemen in the league. He plays a lot of minutes, plays physical, he’s got an unlimited tank. He plays every situation, can do anything you ask of him.” How good would Carlson look in Flyers orange? It could have happened.

4. FUTURE VEZINA WINNER DEALT
Date: June 22, 2012Deal: Flyers trade G Sergei Bobrovsky to Columbus for 2012 second-round pick (45th overall), 2012 fourth-round pick (117th overall) and and 2013 fourth-round pick.Analysis: The Shakespeare play titled “All’s Well That Ends Well” applies here because two trades in 9 ½ months with Columbus led to two backups making the most out of fresh starts, Steve Mason with the Flyers and Bobrovsky for the Blue Jackets. But if Holmgren hadn’t hit the jackpot with Mason, who had struggled badly for four seasons after being the league's Rookie of the Year in 2008-09, he’d have never heard the end of getting so little for Bobrovsky, who blossomed into a Vezina Trophy winner his first season in Columbus. At the time of the trade though, it was obvious that the Flyers would be best served dealing Bobrovsky because they still were committed to Bryzgalov and the two Russian netminders didn’t work together well. The Bobrovsky trade didn’t look bad when it was made because the Flyers got back three fairly high draft picks, a No. 2 and two No. 4s. The Flyers landed a pretty good goalie prospect with the second-round pick they received from Columbus, Jersey product Anthony Stolarz. With one of the fourth-round picks they landed another decent prospect in forward Taylor Leier. Again, the Flyers really got lucky how this saga played out, but what’s alarming is Holmgren and his staff didn’t see Bobrovsky turning into what he became so soon after leaving the organization.

5. CAP MOVE GONE BAD
Date: July 19, 2010Deal: Flyers trade RW Simon Gagne to Tampa Bay for Matt Walker and 2011 fourth-round pick.Analysis: The Flyers needed to shed salary the summer after their trip to the 2010 Stanley Cup Final, and they accomplished that dealing Gagne to Tampa Bay. The problem here is that the Flyers took back a guy who offered them absolutely nothing except his crutch of a contract, three seasons at a $1.7 million cap hit. Walker ended up being an expensive AHL player for one season, then spent most of the other two on the long-term injured list. In his three seasons with the Flyers, he played a total of eight games – four each in 2010-11 and 2011-12. On the day of the trade, Holmgren talked up Walker: "We like the way Matt plays. He's a character-intense player. He plays physical. He's a stay-at-home guy that is a good penalty killer. On our team he can buy us dirty minutes and not be a liability, but be a positive force and help and defend our own zone." The Flyers got none of that. To be fair here, Holmgren’s hands were tied somewhat with Gagne, who supposedly only was willing to waive his no-trade to go to Tampa Bay. With the Flyers over the cap and needing to shed money ASAP, Holmgren pretty much had no choice but to take the best deal he could for Gagne, who was well past his 40-goals-a-year prime and had a year remaining on a contract that carried a $5.25 cap hit. Holmgren would have been better off trading Gagne for a low draft pick.

6. VERSTEEG FOR NO. 1 & NO. 3
Date: Feb. 14, 2011Deal: Flyers acquire LW Kris Versteeg from Toronto for 2011 first-round pick (25th overall) and 2011 third-round pick (85th overall).Analysis: When Versteeg was being traded from team to team early into his career, there were whispers that this multi-talented winger was a bad fit everywhere he went and that his attitude wasn’t great. Describing his half-season in Toronto, Versteeg once was quoted saying, “They said how I was a screw that didn't fit their screwdriver.” The Flyers were Versteeg's third team in a span of three seasons. Although Holmgren gave up two high picks to get Versteeg two weeks before the 2011 trade deadline, the Flyers traded him after the season to create cap space for free agent Jaromir Jagr. The Flyers ended up getting back second- and third-round picks when dealing Versteeg to Florida on July 1, 2011. When looking at both Versteeg trades, the Flyers basically swapped a No. 1 for a No. 2 , but they used the third-round pick that they received from Florida to take D Shayne Gostisbehere, now a highly regarded prospect.

7. BEAM ME OUT, SCOTTIE
Date: March 4, 2009Deal: Flyers traded LW Scottie Upshall and a 2011 second-round pick 2nd round pick for Dan Carcillo.Analysis: On NHL trade-deadline day 2009, the Flyers dumped $900,000 in salary dealing Upshall for Carcillo with the hope of creating cap space to make a bigger deal for a top-pair defenseman. But with the asking price too high, Holmgren struck out trying to pry Jay Bouwmeester from Florida. The Flyers missed Upshall, a heart-and-soul player with speed who did a lot of hitting, worked the corners well and provided some offense as a third-line winger. Carcillo had his moments scoring some big goals during his short time with the Flyers, but he was an agitator who also took a lot of untimely penalties. Maybe the Flyers don’t lose to Pittsburgh in the first round of the 2009 playoffs if Carcillo doesn’t fight Max Talbot with his team up 3-0 in the second period of Game 6. Carcillo won the fight, but Talbot ignited his teammates. The Penguins scored 14 seconds after the fight, rallied for a series-clinching win and went on to win the Stanley Cup.

8. BIG NAME, NO GAME
Date: Feb. 18, 2012Deal: Flyers acquire D Pavel Kubina from Tampa Bay for AHL LW Jon Kalinski, a 2013 second-round pick and a 2013 fourth-round pick.Analysis: In his heyday, Kubina really could play. He was big and strong at 6-foot, 260 pounds, and his booming shot from the point made him a big-time threat on power plays. By the time the Flyers got the Czech though, his best days were over. Holmgren didn’t do his homework here because the Flyers gave up two valuable draft picks and got back nothing close to the guy who scored 17 goals for the 2003-04 Tampa Bay Lightning, who won the Cup that season. In 17 regular season and five playoff games as a Flyer, Kubina was more of a liability than an asset. This was his final NHL hurrah, as the next season he played three games in a Swiss league before retiring in December 2013 at age 35.

9. A HAUNTING TRADE
Date: Dec. 18, 2007Deal: Flyers trade LW Ben Eager to Chicago for D Jim Vandermeer.Analysis: The Flyers had Vandermeer, traded him to Chicago, then made a deal to get him back from the Blackhawks almost four years ago. Bad move. Well, sending Eager the other way sure turned out bad. Although not much of a scorer, Eager is a big guy who could skate up and down the ice pretty well, and that’s how he scored the game-winning goal against the Flyers in Game 2 of the 2010 Stanley Cup Final. Marian Hossa scored 17:09 into the second period to make it 1-0 Chicago, then 18 seconds later Eager blasted a wrist shot past Flyers goalie Michael Leighton from the top of the right circle during a rush. The Blackhawks ended up winning the game 2-1 for a 2-0 series lead and they went onto win the Cup in six games.

WATCH EAGER'S GOAL THAT WON GAME 2 OF 2010 STANLEY CUP FINAL

10. MODRY TRADE
Date: Feb. 19, 2008Deal: Flyers trade 2008 third-round pick (88th overall) to Los Angeles for D Jaroslav Modry.Analysis: Wanting to load up for the stretch run, the Flyers gave up a fairly high draft choice for a veteran defenseman who really struggled. Traded eight days before his 37th birthday, the Czech was a minus-11 for the Flyers in 19 regular-season games, then a minus-6 over nine playoff games. By then, the 6-foot-2, 220-pounder was a poor skater and done. In fact, those Flyers games were his last NHL games, as he finished his career playing four seasons in the Czech League. The Kings didn't use the third-round pick they received from the Flyers wisely taking left wing Geordie Wudrick, who never made it to the NHL. But a few picks later, goalie Braden Holtby, forward Dale Weise and defenseman T.J. Brodie were drafted.